Water → Methyl 2-(7,7,8,8,8-pentafluorooctyl)-8-nonenoate
Reaction equation
[CH2:1]([C:8]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])(C(OC)=O)[C:9]([O:11][CH3:12])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].O.[Cl-].[Li+].CCCCCC.C(OCC)(=O)C>CS(C)=O>[F:28][C:23]([F:29])([C:24]([F:25])([F:26])[F:27])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7])[C:9]([O:11][CH3:12])=[O:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 180 °C
Procedure
Dimethyl 2-hept-6-enyl-2-(7,7,8,8,8-pentafluorooctyl)propan- 1,3-dioate(9.31 g, 21.62 mmol) prepared in Step 4 was dissolved in anhydrous DMSO(100 ml), water(0.39 ml, 21.62 mmol) and lithium chloride(1.82 g, 43.25 mmol) were added, and the resulting mixture was stirred for 4 hours at 180° C. The reaction mixture was cooled to room temperature, extracted with ethyl acetate, washed with distilled water, and dried over anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure and the residue was purified by column chromatography(eluent:n-hexane/ethyl acetate=50/1, v/v) to give 4.46 g(Yield 55.4%) of the title compound as a colorless oil.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- extractionextracted with ethyl acetate
- washwashed with distilled water
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was removed by concentration under reduced pressure
- customthe residue was purified by column chromatography(eluent
Sources & evidence
- ORD record
- ord-15959931e045468d84c09ffee819e5c3
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06555571B2
Reaction notes
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